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Synfacts 2015; 11(1): 0072
DOI: 10.1055/s-0034-1379646
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cyclization of 1-(Trifluoromethyl)-4-alkyn-1-ones with Arylboronic Acids

Contributor(s):
Paul Knochel
,
Diana Haas
Johnson T, Choo K.-L, Lautens M * University of Toronto, Canada
Rhodium-Catalyzed Arylative Cyclization for the Enantioselective Synthesis of (Trifluoromethyl)cyclobutanols.

Chem. Eur. J. 2014;
20: 14194-14197
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Further Information

Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

boronic acids - cyclization - rhodium

Significance

Lautens and co-workers report a rhodium-catalyzed cyclization of 1-(trifluoromethyl)-4-alkyn-1-ones with variously substituted arylboronic acids to obtain (trifluoromethyl)cyclobutanols bearing an exocyclic double bond.


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Comment

The reactivity of the newly formed exocyclic double bond was explored by subjecting a (trifluoromethyl)cyclobutanol to an epoxidation reaction using MCPBA and an ozonolysis.


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